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Triethylamine → Methanesulfonic acid 4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl ester

HRID 480116
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 480116
[OH:1][C:2]12[CH2:9][CH2:8][C:5]([C:10]3[NH:18][C:17]4[C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH3:22])[C:14](=[O:23])[N:13]([CH2:24][CH2:25][CH3:26])[C:12]=4[N:11]=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.CCN(CC)CC.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[O:23]=[C:14]1[N:13]([CH2:24][CH2:25][CH3:26])[C:12]2[N:11]=[C:10]([C:5]34[CH2:8][CH2:9][C:2]([O:1][S:35]([CH3:34])(=[O:37])=[O:36])([CH2:7][CH2:6]3)[CH2:3][CH2:4]4)[NH:18][C:17]=2[C:16](=[O:19])[N:15]1[CH2:20][CH2:21][CH3:22]
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 99507768-(4-hydroxybicyclo[2.2.2]octan-1-yl)-1,3-dipropyl-1H-purine-2,6(3H,7H)-dione

Produkt 1

HCID 86591739Methanesulfonic acid 4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl esterAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of 50 mg of 8-(4-Hydroxy-bicyclo[2.2.2]oct-1-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (Example 13a) (0.14 mmol) in CH2Cl2 (5 ml) was added 20 μL of Et3N and the reaction mixture cooled in an ice bath. To this was added 20 μL of methanesulfonyl chloride (0.26 mmol) and the reaction mixture kept at 10° C. overnight. The reaction mixture was concentrated in vacuo and the residue taken up in EtOAc and washed 2× with dilute HCl (5 ml). The organic layer was dried over NaSO4 and conc'd. The residue was triturated in acetonitrile to afford 36 mg (59%) of pure white solid (MH+=439.4).

Aufarbeitung

  1. temperaturethe reaction mixture cooled in an ice bath
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. washwashed 2× with dilute HCl (5 ml)
  4. dry with materialThe organic layer was dried over NaSO4 and conc'd
  5. customThe residue was triturated in acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-520dcee7e5894143af209ac4b0c1b0b8
Quelldatensatz
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06649600B1

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